The release of embarrassing e-mails portraying the Spanish king's son-in-law as a sexist and ungallant character has capped a bad week for the embattled royal, who has also seen various properties confiscated in a corruption inquiry.
On Friday, the satirical magazine Mongolia published the latest in a series of e-mails that have emerged from the royal household, heaping yet more damage on an already tarnished brand.
In them, the king's son-in-law, Inaki Urdangarin, is seen mocking his own sister-in-law, revelling in base, sexist humour, and laughing at the expense of his royal relatives.
The release came days after a judge confiscated half of a palace and various other villas that Urdangarin, the Duke of Palma de Mallorca, owns with his wife, La Infanta Cristina, the king's youngest daughter.
The assets were to be held as bail in an ongoing investigation into allegations that Urdangarin, 45, and his one-time business partner exploited his royal connections to embezzle €6 million (HK$62 million) in public funds.
Cristina, who has yet to face any charges, may yet find herself summoned before a judge after documents showed she signed herself as both landlord and tenant on the palace. The royal family denies any part in alleged wrongdoing.
Urdangarin, a former Olympic medal-winning handball player, was once held up as the bright, shiny new face of the modern royal family. He married Cristina in 1997. But since charges were first brought against him in 2011, nothing has gone right.
In the latest e-mails, which date back to 2003-2004, he forwarded on an obscene joke about his sister-in-law, Letizia, who is married to the next in line to the throne, Crown Prince Felipe. In another e-mail, published by the El Mundo newspaper, he suggests Letizia, a former television news presenter, was enjoying a "royal orgasm".
One of the e-mails, which he mostly sent either to his wife or a group of old friends, mocks women's intelligence by suggesting that an ironing board is the female equivalent of a computer.
In another he says that he is considering going to work for the United Nations' refugee agency and attaches a picture of the people he will be working with. The photo is of a group of semi-naked women.
Earlier this year, Urdangarin, who denies the charges against him, petitioned a court in Barcelona to prevent the publication of his private e-mails. His petition was rejected.